Mineral oil composition



Patented July 19, 1949 UNITED STATES TENT OFFICE v MINERAL OILCOMPOSITION Solomon Caplan, New York, N. Y., and Peter L. Rosamilia,Newark, N. 3., assignors to The Harvel Corporation, a corporation of NewJersey No Drawing. Application December 5, 1945, Serial No. 633,045

Claims. 1

This invention relates to improving hydrocar- L bon oils andparticularly the hydrocarbon mineral oils known as petroleum oils. Inits more specific aspect the invention is directed to improving amineral hydrocarbon oil by adding thereto an ether of hydrogenatedcardanol.

The petroleum oils with which this invention is concerned are the crudeor refined petroleum oils as well as those fractions thereof which haveflash points no lower than 250 F. The oils, whether crude or refinedpetroleum oils or fractions thereof and having ilash points above 250 F.find particular application in the arts of lubrication and electricalinsulation. It has long been recognized that these oils sludge whenemployed in these fields, as .motor oils, turbine oils, aviation oils,Diesel oils, transformer oils and the like. One of the main purposes ofthis invention is to eifect'ively reduce sludging by incorporating aquantity of an ether of hydrogenated cardanol into a mineral hydrocarbonoil Whose flash point is no lower than 250 F.

In the course of our experimentations with this problem, we havediscovered that the sludging of said oils may be retarded and in manycases completely inhibited by adding thereto a quantity of an ether ofhydrogenated cardanol. For most purposes the ratio by weight of saidether of hydrogenated cardanol to said 011 may be as low as 1 to 200 andmay be between about 1 to 200 and 2 to 100 although it is also possibleto employ these components in the ratio of about 1 to 1000 and to 100.

Hydrogenated cardanol may be prepared in a number of diiierent ways.Ordinarily it may be produced by recovering a particular distillate ofhydrogenated cashew nut shell liquid. The cashew nut shell liquidemployed as one of the starting ingredients may be the raw cashew nutshell liquid obtained either by the solvent extraction of said liquidfrom said nuts by using a hot cashew nut shell liquid bath as set forthin the S. patent to E. R. Hughes, No. 2,058,456 of October 27, 1936. Itis preferable to first treat the raw cashew nut shell liquid with asmall amount of an acidic agent to remove therefrom any naturallyoccurring metals as set forth in the patents to Harvey et al., Nos.2,128,247 of August 30, 1938, and 2,067,919 of January 19, 1937. The sotreated cashew nut shell liquid has long been known as treated cashewnut shell liquid. This treated cashew nut shell liquid is subjected tohydrogenation treatment in order to completely hydrogenate only theunsaturated side chains of the various phenols therein. Thishydrogenation may be accomplished by following the method set forth inU. S. patent to S. Caplan, No. 2,181,119 of November 28, 1939. Thenafter only the unsaturated side chains of the various phenols in saidcashew nut shell liquid have been completely hydrogenated or saturatedwith hydrogen, this hydrogenated cashew nut shell liquid is subjected todistillation under low pressure conditions. It may be distilled at avapor temperature of 600 F. and at 30 mm. of Hg pressure. Distillationis continued under these conditions until the distillate recovered isbetween about 50% to by weight of the hydrogenated cashew nut shellliquid subjected to this distillation. This recovered distillate ishydrogenated 'cardanol and is a waxy. solid at room temperature,consists essentially of a compound having a boiling point ofapproximately 227 C.-235 C. at 5 mm. of Hg pressure having the followinggeneral formula:

The ethers of hydrogenated cardanol employed in the practice of thisinvention are those ethers in which the hydrogen atom of the OH group ofthe hydrogenated cardanol is replaced by an organic radicle orsubstituent. This substituent may be'either aliphatic, aromatic or acombination of both and is preferably a hydrocarbon radicle, examples ofwhich are methyl, ethyl, amyl, ben'zyl, lauryl, tertiary butyl, etc. Ofthese We prefer that the hydrocarbon radicle be a primary, secondary ortertiary alkyl radicle.

These ethers may be produced in the manner set forth in the patent to S.Caplan, No. 2,181,119 of November 28, 1939. Generally, they may beproduced by heating a mixture of approximately 300 grams of hydrogenatedcardanol, 45 grams of NaOH in grams of water and a molecular equivalentof a halide or sulphate of the organic radicle which is to replace thehydrogen of the CH of hydrogenated cardanol. The mass is maintained at atemperature of about 100 C. until the reaction mixture is practicallyneutral and until a sample which is dehydrated and neutralized issubstantially insoluble in three volumes of alcohol. After the reactionhas been consummated, the ether is separated from the remainder of thereaction mass. By following this general procedure the various ethers ofhydrogenated cardanol may be readily and easily produced.

The following specific comparative tests indi- 3 cate the effectivenessof the ethers of hydrogenated cardanol as sludge inhibitors in petroleumoils.

Into each of four 400 cc. beakers was poured 200 grams of a petroleumoil known on the market as Wemco C and having a flash point above 260 F.and generally employed as a transformer oil. At this time the oil was:clear and free of sludge. To the oil in only three of said beakers wereadded respectively 4 grams of the benzyl ether of hydrogenated cardanol,the amyl ether of hydrogenated cardanol and the ethyl ether ofhydrogenated cardanol, which was stirred therein whereupon solution tookplace. Then all four of these beakers together with their contents wereplaced in an oven at 300 F. for a period of 96 hours. At the end of thisperiod they were removed from the oven and the following results wereobtained: The control beaker containing only the petroleum oil wasexamined and the oil therein was cloudy and turbid and a clearly visiblesludgy mass or precipitate had deposited out'on the bottom of thebeaker. The beaker containing the solution of petroleum oil and theethyl ether of hydrogenated cardanol showed a greatly reduced sludgingmeasuring about 25% of that of the control whereas the oil in thebeakers containing the benzyl or amyl ether of hydrogenated cardanol wasexamined and found to be clear and showed no evidence of sludging. Atthe end of this 96 hour period, the power factor of the contents of eachof said four beakers was determined and it was found that the powerfactor of each of said ether-hydrocarbon oil solutions was no greaterthan that of the oil itself.

'Into'each of four 400 cc. beakers was poured 200 grams of a petroleumoil known on the market as Havoline No. 10-free of additives and havinga flash point between 540 EL-600 F. and generally known and employed asa motor lubricating oil. At this time the oil was clear and free ofsludge. To the oil in only three of said beakers were added respectively4 grams of benzyl ether of hydrogenated cardanol, amyl ether ofhydrogenated cardanol, and ethyl ether of hydrogenated cardanol, whichwere stirred therein whereupon solution took place. Then all four ofthese beakers together with their contents were placed in an oven at 300F. for a period of 168 hours. At the end of this period they wereremoved from the oven and the following results were obtained: Thecontrol beaker containing only the petroleum oil was examined and theoil therein was cloudy and turbid and a clearly visible sludgy mass orprecipitate had deposited out on the bottom of the beaker. The beakerscontaining the solution of petroleum oil and the benzyl, amyl or ethylethers of hydrogenated cardanol were examined and the oil containingNumber the benzyl ether of hydrogenated cardanol as well as the 011containing the amyl ether of hydrogenated cardanol showed greatlyreduced sludging measuring about 25 of that of the control samplewhereas the oil containing the ethyl ether of hydrogenated cardanol wasfound to be clear and showed no evidence whatever of sludging.

Besides improving said oils to decrease their tendency to sludge, theincorporation of an ether of hydrogenated cardanol in said oils improvesthe quality of greases made therewith. The various greases may be madeby heat dissolving or dispersing a soap, such as sodium stearate,aluminum stearate or the like in said combination of mineral oil and anether of hydrogenated cardanol and then cooling said mass.

Having thus described our invention, what we claim and desire to haveprotected by Letters Patent is:

l. A hydrocarbon ether of hydrogenated cardanol dissolved in a mineralhydrocarbon oil whose flash point is above 250 F. said other beingpresent in small amounts, sufficient to inhibit sludging of said oil.

2. Methyl ether of hydrogenated cardanol dissolved in a mineralhydrocarbon oil whose flash point is above 250 F. said ether beingpresent in small amounts, sufiicient to inhibit sludging of said oil.

3. Ethyl ether of hydrogenated cardanol dissolved in a mineralhydrocarbon oil whose flash point is above 250 F. said ether beingpresent in small amounts, sufiicient to inhibit sludging of said 011.

4. Amyl ether of hydrogenated card-anol dissolved in a mineralhydrocarbon oil whose flash point is above 250 F. said other beingpresent in small amounts, sufficient to inhibit sludging of said oil.

5. An ether dissolved in a mineral hydrocarbon oil whose flash point isabove 250 F. said other being a hydrocarbon ether of a phenol having a15 carbon atom alkyl substituent the ratio by weight of said other tosaid oil being in the range of 1-1000 to 10-100.

SOLOMON CAPLAN. PETER L. ROSAMILIA.

REFERENCES CITED The following references are of record in the file ofthis patent:

UNITED STATES PATENTS Name Date 2,181,119 Caplan Nov. 28, 1939 2,240,034Caplan Apr. 29, 1941 2,384,323 McCleary Sept. 4, 1945

